N-Heterocyclic carbene-catalyzed enantioselective synthesis of functionalized cyclopentenes via α,β-unsaturated acyl azoliums

N-Heterocyclic carbene-catalyzed enantioselective synthesis of functionalized cyclopentenes via α,β-unsaturated acyl azoliums

Highly enantioselective NHC-organocatalyzed synthesis of functionalized cyclopentenes proceeding via α,β-unsaturated acyl azolium intermediates is reported. The organocascade reaction of modified enals with malonic ester derivatives having a γ-benzoyl group involves the Michael-intramolecular aldol-...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) Vol. 50; no. 93; p. 14539
Main Authors: Mondal, Santigopal, Yetra, Santhivardhana Reddy, Patra, Atanu, Kunte, Sunita S, Gonnade, Rajesh G, Biju, Akkattu T
Format: Journal Article
Language:English
Published: England 04-12-2014
Subjects:
Azo Compounds - chemistry
Carbolines - chemistry
Catalysis
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Heterocyclic Compounds - chemistry
Molecular Structure
Stereoisomerism
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Summary:Highly enantioselective NHC-organocatalyzed synthesis of functionalized cyclopentenes proceeding via α,β-unsaturated acyl azolium intermediates is reported. The organocascade reaction of modified enals with malonic ester derivatives having a γ-benzoyl group involves the Michael-intramolecular aldol-β-lactonization-decarboxylation sequence to deliver cyclopentenes in good yields and excellent ee values.
ISSN:1364-548X
DOI:10.1039/c4cc07433e